BOC-(R)-3-BROMO-4-HYDROXYPHENYLGLYCINE

Base Information

• Chemical Name: BOC-(R)-3-BROMO-4-HYDROXYPHENYLGLYCINE
• CAS No.: 139517-62-7
• Molecular Formula: C₁₃H₁₆BrNO₅
• Molecular Weight: 346.178
• Mol file: 139517-62-7.mol

Synonyms:(2R)-2-(3-bromo-4-hydroxyphenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]acetic acid

Chemical Property of BOC-(R)-3-BROMO-4-HYDROXYPHENYLGLYCINE

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of BOC-(R)-3-BROMO-4-HYDROXYPHENYLGLYCINE

There total 8 articles about BOC-(R)-3-BROMO-4-HYDROXYPHENYLGLYCINE which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

methyl (2R)-2-(3-bromo-4-hydroxyphenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]acetate (162458-72-2) → (2R)-2-(3-bromo-4-hydroxyphenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]acetic acid (139517-62-7)

Guidance literature:

methyl (2R)-2-(3-bromo-4-hydroxyphenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]acetate; With lithium hydroxide monohydrate; In tetrahydrofuran; water; at 25 ℃; for 16h;

With hydrogenchloride; In water; pH=4;

DOI:10.1021/acs.jmedchem.1c00034

Reference yield: 94.0%

(R)-3-bromo-4-hydroxyphenylglycine hydrobromide + di-tert-butyl dicarbonate (24424-99-5) → (2R)-2-(3-bromo-4-hydroxyphenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]acetic acid (139517-62-7)

Guidance literature:

With sodium hydroxide; In tert-butyl alcohol; at 20 ℃; for 1h; pH=9;

DOI:10.1021/jo0621266

Reference yield:

D-4-hydroxyphenylglycine (22818-40-2) → (2R)-2-(3-bromo-4-hydroxyphenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]acetic acid (139517-62-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 67 percent / bromine / acetic acid / 24 h / 20 °C

2: 94 percent / aq. NaOH / 2-methyl-propan-2-ol / 1 h / 20 °C / pH 9

With sodium hydroxide; bromine; In acetic acid; tert-butyl alcohol;

DOI:10.1021/jo0621266

upstream raw materials:

di-tert-butyl dicarbonate

D-4-hydroxyphenylglycine

(S)-hydroxyphenylglycine

D-2-p-hydroxyphenylglycine methyl ester

Downstream raw materials:

methyl (R)-N-(tert-butoxycarbonyl)-2-(3-bromo-4-methoxyphenyl)glycinate

<(R)-(3-bromo-4-methoxyphenyl)-N-tert-butoxycarbonylglycyl>-(S)-alanine methyl ester

C₃₉H₄₉BrN₄O₁₃Si

C₃₉H₄₉BrClN₃O₁₁Si

Refernces

• 1、 Becker, Dominic,Kazmaier, Uli. "Synthesis of simplified halogenated chondramide derivatives with strong cytostatic properties". . p. 2591 - 2602. Retrieved 2015/04/27.
• 2、 Prieto, Monica,Mayor, Silvia,Rodriguez, Katy,Lloyd-Williams, Paul,Giralt, Ernest. "Racemization in Suzuki couplings: A quantitative study using 4-hydroxyphenylglycine and tyrosine derivatives as probe molecules". . p. 1047 - 1050. Retrieved 2008/02/04.